


Hands Are Clever

by DRHPaints



Category: Conan O’Brien, Conan O’Brien RPF, Late Night Host RPF, US Comedians RPF
Genre: Blow Jobs, Cunnilingus, Explicit Language, Explicit Sexual Content, F/M, Hand Jobs, Massage, One Shot, Smut, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2020-09-21
Updated: 2020-09-21
Packaged: 2021-03-08 00:27:21
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,109
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26586601
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: Conan treats himself to a massage after a long few weeks of filming. When he gets hard, things with massage therapist Ruby get into, and out of, hand.
Relationships: Conan O’Brien/Original Female Character
Kudos: 5





	Hands Are Clever

**Author's Note:**

  * For [damn_conan](https://archiveofourown.org/users/damn_conan/gifts).



> For those who are curious the title comes from a song of the same name by Alex Clare.

Sitting in the waiting area, Conan flipped through a magazine that was at least three months old, one lanky leg crossed over his knee, foot jiggling.

“Mr. O’Brien?” A tall, curvaceous woman in black leggings and a green tank under a flowing black blouse appeared in the doorway, mass of crimson waves piled atop her head.

“Yes.” Conan grinned, standing and shaking her outstretched hand.

“Hi, I’m Ruby. I’ll be your massage therapist today.” 

Nodding, Conan’s orange hair bounced. “Hey Ruby.” 

Smiling, Ruby led him down the hall and Conan couldn’t help but notice the pleasant heart shape of her ass, panty lines clearly visible as her hips switched and she gestured to an open door. “Alright, Mr. O’Brien.” Conan noticed how her voice softened as they passed the threshold, instantly becoming low and soothing. “I’m going to step out for a couple of minutes. If you would like to get undressed, then lay beneath the sheet.” Ruby indicated the fabric draped across the table. “I’ll be right back.”

“Great, thank you.” With a little wave Ruby left and Conan pulled his Guinness shirt overhead, placing it on the chair as he toed off his shoes and undid his skinny jeans. Once naked, he looked at the table questioningly. Ruby didn’t say whether he should be face up or face down. Deciding to lay on his stomach, Conan adjusted the sheet over his lower back, resting on his folded arms, long body dangling well off the table's edge as he waited.

Moments later a knock came at the door. “Are you ready, sir?”

“Yes.” Conan called out, chin on his wrists.

Entering with a warm smile, Ruby pressed play on a music station and the room filled with subtle, tinkling, vague new-agey music that always made Conan wonder if every massage establishment was issued the same album.

“Alright.” Affecting the same relaxing voice, Conan noticed Ruby squeezing oil over her elegant ivory hands and the scent of lavender wafted over him. “Are there any particular areas you’d like me to concentrate on?”

“The center of my spine has been acting up.” Awkwardly bending his arm back, Conan pointed at himself. “And also my left quadricep, up near the hip.”

Ruby nodded. “Sounds good. Okay, now rest your face in the opening and relax.” 

Shifting himself down a bit, Conan put his head in the hole, arms at his sides. “I apologize if my hands are cold. You’re my first massage of the day, but they should warm up soon.” Ruby intoned as she placed her fingers alongside his neck.

“No, they’re fine.” Starting tenderly, Ruby’s hands touched Conan’s tense flesh, rubbing in languid, precise circles.

Leaning over him, Ruby tilted her head. “How’s the pressure? Softer? Harder?”

“Harder, please.” After an arduous few weeks of the new season, Conan was treating himself. It wasn’t often he sprang for a massage. Frankly, Conan didn’t usually have the time. But today he carved out an entire afternoon for himself, booking a luxurious two hours, and for Conan to get the gorgeous Ruby as his therapist, well, that was just a bonus.

“No problem.” Kneading his aching muscles, Ruby bent her elbows and dug forward. Obviously, seeing the name on the books, Ruby knew who to expect when she came into work that morning. Ruby had been a fan for ages, but working in LA she learned quickly to be professional and treat every client, no matter their stature, with respect and anonymity. But if she was honest, there was a part of Ruby that over the years found Conan more than a little sexy as she watched the silly late night comedy man dance about and sling his jokes. So now, for her hands to be passing over his skin, truly as pallid and freckle-strewn as he constantly claimed, was exciting.

Reaching the center of his back, when Ruby bore down and unwound the persistent knot that had Conan stretching himself over the back of his chair during commercial breaks for the past two weeks, he released an inadvertent groan.

“Everything alright?” Ruby murmured softly.

“Yeah.” Conan exhaled. “That felt amazing.”

Grinning, Ruby applied more oil to her hands before making a second pass. “Oh good.”

“Yeah.” Conan chuckled lightly. “Obviously telling stupid jokes to a crowd that’s just there for the free air conditioning is really back-breaking work.”

Ruby laughed. “Oh, come on. I’m sure you work very hard.” Rubbing his shoulder in a consoling, rather than massaging way, Conan popped his head up and turned back to her. Ruby removed her hand, blinking.

Face spreading into a smile, Conan nodded. “Thank you.”

Grinning, Ruby shrugged and Conan resumed his position. Completing his back, she began massaging Conan’s left arm, impressed by the light muscling that wasn’t readily apparent on screen. Working her way down to his large freckled hand, there was something intrinsically intimate about interlacing their fingers, squeezing over his lengthy digits, and Ruby caught herself biting her lip, holding on and caressing perhaps a little longer than she should have. 

Repeating the other arm, Ruby restrained herself with Conan’s hand this time and moved down to his feet, but immediately as she touched him Conan twitched. “Actually.” He interrupted her. “If you could skip the feet. I’m really ticklish.”

Grounding a smile, Ruby nodded. “No problem.” Starting at his right ankle, Ruby ascended Conan’s lithe legs. As was her custom, Ruby folded up the sheet a few inches at a time, and she marveled at Conan’s stunning alabaster stems. Conan had the legs of a model, or a dancer, lean and seemingly never ending.

Ruby’s fingers dancing up his hamstring, when she raised the sheet until it hovered just below Conan’s tiny ass, agile hands sneaking between his thighs and kneading the space inches from his balls, Conan swallowed. Cock throbbing, Conan didn’t want to get an erection, so he tried to focus his thoughts. Baseball. Roadkill. Jordan Schlansky. But try as he might, Conan’s brain kept nudging him with the image of Ruby’s ass, the shape of her red-stained mouth, what it might look like around him, and despite his protests, Conan’s cock thickened below his body.

Moving to the other leg, Ruby paid close attention to the quad Conan mentioned before completing his backside. “Alright.” Breaking the silence in a voice barely above a whisper, Ruby gently rested her fingertips on Conan’s shoulder. “It’s time to turn over.”

Coming to his arms, Conan cleared his throat. “Um…I...I just need a few minutes.”

“Oh?” Ruby furrowed her brow.

“Yeah, um…” Faint skin of his face turning pink, Conan shifted his eyes away. “To...to calm down a bit.”

Gleaning his meaning, Ruby nodded. “Oh, well…” She looked at the clock. “Your time is already more than half over, sir, and…” Trying to keep her tone light, Ruby shrugged. “It happens all the time. Really not a big deal. Don’t worry about it.”

Considering, Conan chewed his lip. “Alright…”

“Okay. I’ll just lift the sheet and you can flip over.” Turning her head away, Ruby hoisted the fabric and Conan rolled onto his back. Lowering it over him, Ruby had to fight to wipe the look of shock off her features. As she said, it was true that her male clients often got erections during a massage. It was only natural, and typically not a big deal.

But Conan was a  _ massive  _ deal. Long, thick cock curved under the beige sheet as he blinked up at the ceiling and Ruby saw his hands trying not fidget at his sides.

Stepping to the top of the table, Ruby tilted her head. “Alright, would you like your scalp done?”

“Yes, please.” Conan nodded. Ruby bent down to rummage below the table for baby wipes to clean the oil from her hands, giving Conan a generous peek at her cleavage as she did so, which certainly wasn’t helping his predicament.

Starting at the nape of his neck, Ruby pulsed her way over Conan’s skull, his crystalline blue eyes falling shut in bliss. As Ruby’s hands flowed, she couldn’t help but play with that iconic ginger hair, weaving it between her fingers, twisting and teasing. Ruby knew Conan might call her on it, might say, ‘Hey, there are no muscles in my fucking hair, what the hell are you doing with it, you creep?’ But she couldn’t resist.

But Ruby’s concerns were alleviated when a deep moan grumbled up from Conan’s chest. “Mmm...that’s nice.” His thin lips uttered as she tugged lightly at his tangerine locks. 

“Good…” Ruby purred. “I’m glad you like it.” Moving on, she brushed her fingers delicately over Conan’s handsome facial features, tracing his prominent cheekbones and tingling between her thighs as she flowed over his sculpted jaw. 

Passing down, Ruby reapplied the oil and her hands trickled over his chest, slicking down the sparse orange body hair as she descended his abdomen, caressing his endearing little belly and drawing dangerously near the column she was trying so hard to ignore as it stood insistently beneath the fabric. 

Going over the tops of his legs, when Ruby dug into his injured hip, Conan winced and she backed off. “Oh, sorry.”

“That’s okay.” He shook his head. 

“Can I ask,” Ruby narrowed her eyes as she resumed with a more tender touch. “How did you hurt the area?”

Mouth spreading into a wide smile, showing off his lovely teeth and crinkling in the corners of his baby blue eyes, Conan chuckled. “Well...I tried to mount a water buffalo and I, uh...fell off and landed hard on the stage.”

Bursting out laughing, Ruby shook her head. “Yeah, that’ll do it.” 

Completing Conan’s top half, Ruby looked at the clock. They still had almost half an hour remaining. She was used to doing 90 minute sessions, and Conan’s decision to skip his feet gave her more time than she realized. Ruby could ask Conan if there were any areas he wanted her to go over again. Or…

“You know…” Fingertips grazing Conan’s upper thigh, Ruby cleared her throat. “If there’s...tension. Anywhere in the body…” Staring at his cock, Ruby's nose flared. “It can be harmful to your entire disposition.”

Blinking up at her, Conan’s face grew warm as he followed Ruby’s line of sight. Swallowing, he shifted a little. “Oh...oh yeah? That...makes sense.”

“Do you want me to…” Emerald eyes flicking up to meet his, Ruby bit her lip. “Make sure you’re not carrying any extra stress?”

Breath hitching, Conan’s tongue darted over his lips. “Yeah. Yeah, okay.”

With a timid glance at the door, Ruby squirted more oil on her hands before tentatively lifting the sheet. Hand creeping underneath, her fingers encircled Conan’s thick cock as she looked into his cerulean eyes.

Conan sharply inhaled as Ruby glided the thin skin up and partially over the head of his cock, her practiced hands strong yet tender as she began jerking him. “How’s that?” Voice changing, it was no longer the cooing, reassuring massage therapist tone, but instead sultry, alluring as Ruby leaned forward.

“Good.” Conan nodded.

Other hand tiptoeing beneath, Ruby began rolling his balls between her agile fingers and Conan’s neck arched, thrusting into her warm hands. “ _ Fuck _ , really good.” Locking back into her gaze, Ruby was mesmerized by his oceanic eyes as her hands moved under the sheet and, curiosity getting the better of her, decided to be bold.

“Can I…” She gestured with her head toward his lap. “Can I look?”

Nodding, Conan pulled back the fabric, and his cock was just as beautiful as it felt, swollen almost purple now with Ruby’s ministrations as she firmly pressed the ball of her thumb into Conan’s frenulum and rotated. 

Groaning in delight, Conan lifted an anxious hand, fingers brushing Ruby’s forearm. “Would you…” Gritting his teeth, the muscles in Conan’s jaw jumped. “Would you let me see you? Maybe?” 

Blue eyes looking hungrily at her chest, Ruby glanced down and nodded. “Okay.” Dropping his cock, she peeled her shirt and sports bra overhead, exposing her ample breasts and Conan folded his lips under, staring as Ruby took him in hand once more.

Conan squirmed on the table top, rutting his hips forward and exhaling mewls of ecstasy as he lost himself in Ruby’s frenzied fingers. “Fuck...yes, that feels so good.” 

Seeing his arousal, Conan’s noises proving too much, Ruby made a decision. “Do you...you want me to suck you?”

“Oh fuck yes.” Conan nodded insistently and without pretext Ruby bent over the table and sank her mouth over him, taking half of Conan’s length down her throat and hollowing her cheeks.

“Oh.. _ fuck, fuck…”  _ Conan gasped, one hand gripping the edge of the table while the other snatched at Ruby’s bun. Bobbing fast and stroking his shaft to her lips, the taste of the oil was mildly bitter but Ruby didn't mind as she continued fondling Conn’s balls and he began rolling his hips. With three fingers, Ruby began massaging small circles into the space directly behind Conan’s balls. And when Conan yelped, nearly sitting up on the table before his sizable hand forced her down on his substantial cock, Ruby’s lips smiled around him as she dug up to stimulate his prostate externally and continued to suck. 

Moans rising to whimpers, Conan’s feet flexed in the air and he shook his head. “Would…” He panted, fingers reaching down to cup Ruby’s face. “Would you let me fuck you?”

Emerging with a theatrical pop, Ruby met his stormy blue eyes and nodded. “Yes. Fuck me, Conan.” Slipping her leggings and panties to the floor, Ruby kicked them away as Conan crawled from the table and approached her, taking Ruby’s face in both of his large hands and joining their mouths. Thin lips moving against her as their tongues wound together, Conan pressed Ruby back to the table and she climbed on, one of Conan’s hands snaking between her thighs to twirl her clit.

As she lay on the table, Conan bent over her, his fingers coaxing Ruby to ecstasy, she nearly laughed at the role reversal before Conan started brushing his lips over the sensitive skin of her neck, kissing his way down her body. Drawing a nipple into his mouth, Conan’s strong hands caressed her breast before he parked between her legs, clamping his fingers around Ruby’s hips and dragging her forcibly to the edge of the table.

Edging his sharp jaw forward, Conan spread Ruby open with two fingers, rejoicing in how wet she was and reveling in her flavor as he lapped at her swollen clit. Ruby’s hands reached for Conan, one combing through his apricot hair while the other, through some innate habit, began massaging at the spot where his neck joined his shoulder while he consumed her. “ _ Oh Conan! Yes Fuck!” _ Moaning, Ruby rocked forward into his eager tongue, heels braced on the table’s edge. Relentless, Conan took her clit between his slender lips and sucked, causing Ruby’s pelvis to rise from the table’s surface at the same level as her shrieks, forcing Conan to extend a long arm and cover her mouth, vice-like as Ruby screamed into his fingers.

Tearing at his hair, Ruby humped Conan’s mouth with abandon as her warm breath condensated the lower half of her face under the cover of Conan’s hand. Shaking, Ruby’s feet slipped from the table and her eyelids fluttered as she came, muffled screams trapped in her throat as Conan emerged.

Wiping his face on his arm, Conan climbed up to join Ruby on the table, lowering himself and combing back her hair. “Hey, um…” One of his long fingers traced her lower lip. “I don’t have a condom.”

“I’m on the pill.” Ruby nodded. “Don’t worry about it.”

“Okay.” Smiling, Conan smeared his cock over her entrance. “Ready?”

Ruby nodded and Conan tipped his hips forward, entering her with a groan as he was enveloped by the warm wetness. “Ah... _ fuck,  _ Ruby,  _ yes.” _

Capturing his lips, Ruby knit their tongues together as Conan wedged an arm between them to spin his thumb over her clit, carefully coming to a knee and lifting Ruby’s leg over his waist. Swiveling inside of her, Ruby planted her feet on the table, rushing to meet his pounding hips as Conan’s thick cock spread her open. “ _ Oh Conan! Yes! Just like that! _ ” Ruby cried as he hammered into the sensitive patch of nerves, causing her eyes to twitch and her thighs to quake. 

“Yeah, is that good?” Conan’s reedy voice breathed as he pounded into Ruby, table creaking menacingly beneath them. “Am I going to make you cum? Huh? You like the way I fuck you, don’t you?”

“ _ Yes, I love it! Fuck me, Conan! Yes! Fuck! _ ” Ruby breathed, hands clasped around his neck and holding his forehead to hers as she frantically rutted her pelvis against him.

Smirking, Conan slammed into Ruby recklessly, table legs screeching across the floor. “Are you gonna cum for me?  _ Huh?  _ Are you gonna cum on my cock? I know how badly you want it. I saw you staring, Ruby. You love my cock, don’t you?  _ Don’t you?  _ Cum for me. Cum on my hard cock. Do it, Ruby.  _ Cum for me. _ ”

Voice rising, Ruby smothered her own mouth this time as she fluttered around Conan and her toes curled.

As Ruby constricted around him, she dug her nails into Conan’s shoulders but struggled to find purchase as his skin was still slick with oil, her body convulsing as the whites of her eyes flashed and she dripped a wet spot onto the table. 

Laying flat, Conan buried his face in her neck, skinny lips breathing a moist spot into Ruby’s skin as his body bounced above her. “ _ Oh Ruby! Oh fuck, I’m going to fucking cum inside you! Yes! Fuck! YES! _ ” Conan’s face scrunched, mouth agape as he strained before his hips jumped irregularly and he let out a long whine, filling Ruby with pulsing warm cum before his body stilled.

Laying atop her, skin dewy with a mixture of sweat and oil, Conan brushed a kiss to Ruby’s cheek before rolling off. “Could you hand me some of those?” Ruby gestured to the packet of baby wipes underneath the table and nodding, Conan placed it before her, finding the sight of Ruby using sheet after sheet to clean his sticky white cum from herself deeply erotic as he dressed.

“Well…” Hopping up, Ruby adorned herself once more in her leggings. “I hope you enjoyed your massage.” She grinned at him.

“Yeah.” Conan beamed back at Ruby. “Definitely more relaxed.”

**Author's Note:**

> Thank you for taking the time to read! If you enjoyed this story, please leave a comment or come say hi on tumblr at fandomtransmandom. I also take requests!


End file.
